Abstract
Lesquerella gordonii (Gray) Wats andLimnanthes alba Benth. (Meadowfoam) are species being studied as new and alternative crops. Triglyceride oil from lesquerella contains 55–60% of the uncommon 14-hydroxy-cis-11-eicosenoic acid. Meadowfoam oil has 95% uncommon acids, includingca. 60%cis-5-eicosenoic acid. Both oils are predominantly unsaturated (3% saturated acids), and have similar iodine values (90–91), from which oxirane values of 5.7% are possible for the fully epoxidized oils. Each oil was epoxidized withm-chloro-peroxybenzoic acid, and oxirane values were 5.0% (lesquerella) and 5.2% (meadowfoam). The epoxy acid composition of each product was examined by gas chromatography of the methyl esters, which showed that epoxidizedL. gordonii oil contained 55% 11,12-epoxy-14-hydroxyeicosanoic acid, and epoxidized meadowfoam oil contained 63% 5,6-epoxyeicosanoic acid, as expected for normal complete epoxidation. Mass spectrometry of trimethylsilyloxy derivatives of polyols, prepared from the epoxidized esters, confirmed the identity of the epoxidation products and the straightforward nature of the epoxidation process. Synthesis and characterization of these interesting epoxy oils and derivatives are discussed.
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References
Carlson, K.D., S.A. Knapp, A.E. Thompson, J.H. Brown and G.D. Jolliff, inYear Book of Agriculture, Chapter 19, U.S.D.A., Washington, D.C., 1992, p. 124.
Chang, S-P.,J. Am. Oil Chem. Soc. 56:855 (1979).
Carlson, K.D., and S-P. Chang, —Ibid., 62:934 (1985).
Kleiman, R., G.F. Spencer and F.R. Earle,Lipids 4:118 (1969).
Smith, Jr., C.R., M.O. Bagby, R.L. Lohmar, C.A. Glass and I.A. Wolff,J. Org. Chem. 25:218 (1960).
Chaudhry, A., R. Kleiman and K.D. Carlson,J. Am. Oil Chem. Soc. 67:863 (1990).
Official Methods and Recommended Practices of the American Oil Chemists' Society, 3rd edn., American Oil Chemists' Society, Champaign, 1983, Method Cd 9-57.
Fioriti, J.A., and R.J. Sims,J. Chromatogr. 32:761 (1968).
Fioriti, J.A., N. Buide and R.J. Sims,J. Am. Oil Chem. Soc. 46:108 (1969).
Miwa, T.K., K.L. Mikolajczak, F.R. Earle and I.A. Wolff,Anal. Chem. 32:1739 (1960).
Miwa, T.K.,J. Am. Oil Chem. Soc., 40:309 (1963).
Kleiman, R., and G.F. Spencer, —Ibid. 50:31 (1973).
Plattner, R.D., H.W. Gardner and R. Kleiman, —Ibid. 60:1298 (1983).
Richter, W.J., and A.L. Burlingame,Chem. Commun. 1158 (1968).
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Carlson, K.D., Kleiman, R. & Bagby, M.O. Epoxidation ofLesquerella andLimnanthes (Meadowfoam) oils. J Am Oil Chem Soc 71, 175–182 (1994). https://doi.org/10.1007/BF02541553
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DOI: https://doi.org/10.1007/BF02541553
Key Words
- Epoxidation
- epoxidized lesquerella oil
- epoxidized meadowfoam oil
- fatty di-
- tri- and tetraols
- GC
- GC-MS
- Lesquerella gordonii
- Limnanthes alba
- meadowfoam
- m-Cl-peroxybenzoic acid
- methyl (5,6,13,14-diepoxy decosanoate
- 5,6-epoxy docosanoate
- 13,14-epoxy docosanoate
- 5,6-epoxy eicosanoate
- 11,12-epoxy-14-hydroxy eicosanoate diastereomers
- TMS derivatives